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Total synthesis and biological evaluation of the resveratrol-derived polyphenol natural products hopeanol and hopeahainol a

Academic Article
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Overview

authors

  • Nicolaou, K.C.
  • Kang, Q.
  • Wu, T. R.
  • Lim, C. S.
  • Chen, D. Y. K.

publication date

  • 2010

journal

  • Journal of the American Chemical Society  Journal

abstract

  • The total synthesis and biological evaluation of the resveratrol-derived natural products hopeanol (2) and hopeahainol A (3) in their racemic and antipodal forms are described. The Friedel-Crafts-based synthetic strategy employed was developed from model studies that established the feasibility of constructing the C(7b) quaternary center through an intramolecular Friedel-Crafts reaction and a Grob-type fragmentation to introduce an obligatory olefinic bond in the growing molecule. The final stages of the synthesis involved an epoxide substrate and an intramolecular Friedel-Crafts reaction, followed by oxidation to afford, upon global deprotection, hopeahainol A (3). The latter was converted under basic conditions to hopeanol (2), whereas the reverse transformation, previously suggested as a step in the biosynthesis of hopeahainol A (3), was not observed under a variety of conditions. Biological evaluation of the synthesized compounds confirmed the reported acetylcholinesterase inhibitory activity of hopeahainol A (3) but not the reported cytotoxic potencies of hopeanol (2).

subject areas

  • Antineoplastic Agents
  • Biological Products
  • Cholinesterase Inhibitors
  • Flavonoids
  • Heterocyclic Compounds with 4 or More Rings
  • Phenols
  • Polyphenols
  • Stilbenes
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Identity

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja102623j

PubMed ID

  • 20462209
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Additional Document Info

start page

  • 7540

end page

  • 7548

volume

  • 132

issue

  • 21

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